Restore checkpoint (“/rewind”) does not work when using “/resume” on a previous chat session. It only works for new chats & stops working once I exit that chat. After exiting a chat, the rewind history is cleared for it.
Steps to Reproduce
Start a chat in the Cursor CLI and make several edits across multiple turns (generating checkpoints).
Exit the session.
Resume that older chat (e.g. agent --resume / select a past conversation).
Try to rewind to an earlier checkpoint.
Result: rewind history is unavailable. Works fine only within a freshly started chat.
Expected Behavior
Rewind restores conversation + workspace to the selected checkpoint, identical to behavior in a live (non-resumed) session.
Operating System
Linux
Version Information
CLI Version: 2026.06.15-03-48-54-da23e37
FYI I’m running the Cursor CLI inside a docker sandbox
For AI issues: which model did you use?
Opus 4.8 1M High Fast
I can reproduce the issue with all models however.
For AI issues: add Request ID with privacy disabled
Hey, thanks for the detailed report with steps and the Request ID. This is a known bug with /rewind after /resume, and it’s already fixed in a newer CLI build.
The tricky part is that even though your version name includes a date (2026.06.15-03-48-54-da23e37), that build is from an older release line, so it doesn’t include the fix yet. Please update the CLI to the latest build:
curl https://cursor.com/install -fsS | bash
Since you’re running the CLI inside a docker sandbox, update it inside the container, or rebuild the image if the CLI is installed during the build step. After updating, check cursor-agent --version and try the /resume + /rewind flow again.
Let me know if the bug still reproduces after the update.
I ran the “/update” command in Cursor CLI to update to the latest Cursor CLI in the Docker Sandbox. The update worked. I tried the behaviour of rewind with resume or new chat for a couple new sessions but it still doesn’t work. Has the bug been fixed fully on this version?
2026.06.15-18-00-12-6f5a2cf
Here is the request-id 2b441a94-770e-4ff2-990a-2b64d894aaef
Hey, thanks for the update and the new Request ID. Since you’re already on a build that should include the fix, and the bug still reproduces, this is on our side and we need to dig deeper. I shared the details internally, but I can’t give an ETA for a fix yet.
To narrow it down, can you confirm a couple of things?
On the new build 2026.06.15-18-00-12-6f5a2cf, does /rewind work in a fresh chat before you exit or run /resume? I want to make sure rewind itself is working.
After /resume, is the rewind list completely empty, or do you see entries but restore doesn’t actually work?
Also about the Docker sandbox. Since /resume can find the old chat, it looks like your CLI data directory persists between sessions. Can you confirm that’s true, meaning the container or volume isn’t being recreated between the sessions you’re resuming?
I got it working now, rewind works well even with old sessions. Thanks for the fix!
As for the docker sandbox, yeah I don’t recreate it and I assume if I did it’d be hard to rewind code changes but the conversation rewind should work, but that’s just my guess.
You can resolve this issue now, but I think the rewind feature is very cool and deserves more rigorous testing from the team in general - just my two cents.
About the Docker sandbox, your guess is correct. Code rewind depends on the file state, so if you recreate the container or volume, it won’t be able to roll the code changes back. Rewinding the conversation itself should still survive a resume.
Thanks for the testing feedback, I’ll pass it to the team. I’m closing this thread as resolved, but if anything comes up again with /rewind, just ping me and we’ll take a look.